(E)-3-[chloro(phenyl)methylene]isobenzofuran-1(3H)-one | 108011-87-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: (E)-3-[chloro(phenyl)methylene]isobenzofuran-1(3H)-one
• 英文别名: ((E)-α-chloro-benzylidene)-phthalide；((E)-α-Chlor-benzyliden)-phthalid；(3E)-3-[chloro(phenyl)methylidene]-2-benzofuran-1-one
• CAS: 108011-87-6
• 化学式: C₁₅H₉ClO₂
• 分子量: 256.688
• InChiKey: NKUMSWJSSBPTBW-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-甲氧基苯硼酸 、 (E)-3-[chloro(phenyl)methylene]isobenzofuran-1(3H)-one 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以62%的产率得到3-[(4-methoxyphenyl)phenylmethylene]-3H-isobenzofuran-1-one
  参考文献：
  名称：

  Copper(II)Chloride-Mediated Cyclization Reaction ofN-Alkoxy-ortho-alkynylbenzamides

  摘要：

  A regioselective intramolecular cyclization/halogenation reaction of N-alkoxy-o-alkynylbenzamides with CuCl2/NCS was developed. The corresponding 3-(chloromethylene)isobenzofuran-1-ones were exclusively obtained via 5-exo-dig cyclization in moderate to excellent yields within 0.5-1 h. This approach has been successfully used to synthesize a biaryl compound by the Suzuki-Miyaura reaction.

  DOI：

  10.1021/ol1029035
• 作为产物：
  描述：

  2-碘苯甲酰胺 在 N-氯代丁二酰亚胺 、 copper(l) iodide 、 四(三苯基膦)钯 、 正丁胺 、 copper dichloride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.0h， 生成 (E)-3-[chloro(phenyl)methylene]isobenzofuran-1(3H)-one
  参考文献：
  名称：

  Copper(II)Chloride-Mediated Cyclization Reaction ofN-Alkoxy-ortho-alkynylbenzamides

  摘要：

  A regioselective intramolecular cyclization/halogenation reaction of N-alkoxy-o-alkynylbenzamides with CuCl2/NCS was developed. The corresponding 3-(chloromethylene)isobenzofuran-1-ones were exclusively obtained via 5-exo-dig cyclization in moderate to excellent yields within 0.5-1 h. This approach has been successfully used to synthesize a biaryl compound by the Suzuki-Miyaura reaction.

  DOI：

  10.1021/ol1029035

文献信息

• Berti; Bernetti, Gazzetta Chimica Italiana, 1957, vol. 87, p. 688,703
  作者：Berti、Bernetti

  DOI：——

  日期：——
• Copper(II)Chloride-Mediated Cyclization Reaction of<i>N</i>-Alkoxy-<i>ortho</i>-alkynylbenzamides
  作者：Manita Jithunsa、Masafumi Ueda、Okiko Miyata

  DOI：10.1021/ol1029035

  日期：2011.2.4

  A regioselective intramolecular cyclization/halogenation reaction of N-alkoxy-o-alkynylbenzamides with CuCl2/NCS was developed. The corresponding 3-(chloromethylene)isobenzofuran-1-ones were exclusively obtained via 5-exo-dig cyclization in moderate to excellent yields within 0.5-1 h. This approach has been successfully used to synthesize a biaryl compound by the Suzuki-Miyaura reaction.